4-(Hydroxymethyl)benzeneboronic acid → HCID 89519193, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (4-(hydroxymethyl)phenyl)boronic acid (2.5 g, 16.8 mmol), 2,2-dichloro-1-((4S,5R)-4-(fluoromethyl)-5-(4-iodophenyl)-2,2-dimethyloxazolidin-3-yl)ethanone (5.0 g, 11.21 mmol) Cs2CO3 (7.3 g, 22.4 mmol) and Pd(PPh3)4 (1.3 g, 1.12 mmol) dioxane (100 mL) and water (30 mL) is heated at 80° C. for 4 hours under nitrogen. Reaction is cooled, washed with water (30 mL), dried over Na2SO4, and concentrated to a syrup. Crude compound adsorbed on celite and purified on silica gel column eluting from 10% to 50% EtOAC/heptane to get the title compound (3.2 g): 1H NMR (400 MHz, CDCl3) δ: (1H NMR) 1.68 (bs, 3H), 1.75 (bs, 3H), 4.50-4.75 (m, 2H), 4.78 (d, 2H, J=6.0 Hz) 4.80-4.87 (m, 0.5H) 5.0-5.13 (br, 1H), 5.14-5.3 (m, 0.5H), 6.2-6.41 (br, 1H), 7.48 (d, 1H, J−8 Hz), 7.53 (d, 1H, J=8.0 Hz), 7.62 (d, 1H, J=8.0 Hz), 7.65 (d, 1H, J=8.0 Hz), (m/z (Cl) 368 [M-(CH3)2CO].

Provenance & Evidence